 Gentry also won the Kentucky Oaks and the Beldame Stakes with Lalun in 1955.In 1964, he sent out the two-year-old Umbrella Fella to win four races including the Breeders' Futurity Stakes

In 1965, Gentry became trainer to John W. Galbreath's Darby Dan Farm.The move forced him to give up training a promising two-year-old named Kauai King who went on to win the following year's Derby.